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Dean Trout began their work experience in 1980 as an Account Executive at Champion Service Corp / Fiserv Cleveland. Dean held this role until 1992. From 1992 to 1995, they served as the VP of IS at Falls Savings Bank. Dean then moved on to work as the VP of IT at Lake Shore Savings Bank from 1995 to 1996. Dean Trout served as the CIO at Signal Bank from 1996 to 1999. Dean then joined Fiserv as an AE from 1999 to 2000. In 2000, they became the SVP and CIO at North Shore Bank. Dean Trout also became a Member of the Fiserv ClearTouch Strategic Planning Council in 2014.

Dean Trout has a background in accounting from Southern Ohio College. It is unclear when they attended the college or if they obtained a degree in accounting. Dean also attended Cuyahoga Falls High School from 1974 to 1977. No degree or field of study information is provided for their time at the University of Akron.